rac-(25R,26R)-25,26-dichloro-5,6,9,14,15,18-hexahydro-5,18:9,14-bis([1,2]benzeno)-6,15-ethanonaphtho[2,3-c]pentaphene | 136954-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: rac-(25R,26R)-25,26-dichloro-5,6,9,14,15,18-hexahydro-5,18:9,14-bis([1,2]benzeno)-6,15-ethanonaphtho[2,3-c]pentaphene
• CAS: 136954-42-2
• 化学式: C₄₄H₂₈Cl₂
• 分子量: 627.612
• InChiKey: WWFWOQOZJXBGFH-OGNXHPTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.47
• 重原子数：
  46.0
• 可旋转键数：
  0.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  rac-(25R,26R)-25,26-dichloro-5,6,9,14,15,18-hexahydro-5,18:9,14-bis([1,2]benzeno)-6,15-ethanonaphtho[2,3-c]pentaphene 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以89%的产率得到5,18:9,14-di<1,2'>benzeno-8,17-etheno-5,8,9,14,17,18-hexahydronaphtho<2,3-c>pentaphene
  参考文献：
  名称：

  Synthesis of three helically chiral iptycenes

  摘要：

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.

  DOI：

  10.1021/jo00024a038
• 作为产物：
  描述：

  反-1,2-二氯乙烯 、 5,18:9,14-di<1',2'>benzeno-5,9,14,18-tetrahydronaphtho<2,3-c>pentaphene 以 萘烷 为溶剂， 反应 48.0h， 以79%的产率得到rac-(25R,26R)-25,26-dichloro-5,6,9,14,15,18-hexahydro-5,18:9,14-bis([1,2]benzeno)-6,15-ethanonaphtho[2,3-c]pentaphene
  参考文献：
  名称：

  Synthesis of three helically chiral iptycenes

  摘要：

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.

  DOI：

  10.1021/jo00024a038